11 cities in 3 months: The highs and lows of digital nomad lifestyle

Written on 6th May, 2015
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In December, my friend and co-worker Brian casually mentioned to me that he would love to go traveling and explore Asia. I love Asia. I lived in Japan as a kid for 3.5 years, and I lived in Hong Kong for 6 months in 2012. It was a no brainer for me to jump on the opportunity and travel around Asia with Brian.

At Buffer, we’re a fully distributed team. We’re currently 31 people spread across 22 cities. We all work remotely, and it is a lot of fun. This also gives us the freedom to choose to be anywhere in the world, and to move or travel if we wish. Everyone is trusted to balance this with their productivity and getting the results for the teams they’re part of.

Being a fully distributed team, we still believe it is super important to meet and spend time with each other face-to-face. As a result, we have team retreats at different locations around the world every 5 months.

In December, our next upcoming retreat was Sydney. The result was that Brian was interested in traveling around Asia, I was keen too, and we had our Sydney retreat coming up. So we decided to spend a month in Asia and ‘travel’ our way to Sydney.

And that’s how it all started for me.

How an idea to travel around Asia turned into being a digital nomad in 11 cities in 3 months

I spent some time thinking and decided to take the plunge and give up my apartment in San Francisco and become a digital nomad with no fixed location. I had been in San Francisco about a year and was craving exploring again, having done a lot of travel in the 4.5 years since starting Buffer (which even contributed to us becoming a distributed team).

It just so happened that I needed to obtain a new US visa (I’ve obtained it now and have the O-1 visa) and I was required to go to a US consulate outside the country to get it, so I decided to make that one of my tasks while in Sydney.

I also had been lucky to be invited to speak on a SXSW panel which got approved, so that was a definite destination for the middle of March in my travel plans. I’ve found through my travels that I really enjoy breaking up long flights, so I chose to spend 2 weeks in Santa Monica to break up my travel to Austin for SXSW. Knowing that I’d only spend a few days in Austin for SXSW, I chose to spend a week in Houston right afterwards to get a more full experience of Texas (my first time in the state!).

All these factors combined, here’s where I ended up spending my time during the first 3 months of 2015:

  • San Francisco, California (May 2014 → Jan 2nd)
  • Tokyo, Japan (Jan 3rd → Jan 11th)
  • Seoul, South Korea (Jan 11th → Jan 18th)
  • Singapore (Jan 18th → Jan 27th)
  • Jakarta, Indonesia (Jan 27th → Jan 28th)
  • Singapore (Jan 28th → Jan 31st)
  • Sydney, Australia (Feb 1st → Mar 3rd)
  • Santa Monica, California (Mar 3rd → Mar 14th)
  • Austin, Texas (Mar 14th → Mar 16th)
  • Houston, Texas (Mar 16th → Mar 21st)
  • Honolulu, Hawaii (Mar 21st → June/July)

I spent time in 11 cities in 3 months, and stayed in 14 different places (2 hotels, 11 AirBnB apartments, 1 friend’s place).

Here’s how that looks on a map:

Why I decided to become a digital nomad again

The last 5 years have included a lot of travel for me. Here’s a rough timeline:

  • October 2010 - July 2011: Birmingham, UK
  • July 2011 - December 2011: San Francisco
  • January 2012 - June 2012: Hong Kong
  • June 2012 - August 2012: Tel Aviv, Israel
  • September 2012 - November 2013: San Francisco
  • December 2013: Traveling around Asia
  • January 2014 - March 2014: San Francisco
  • April 2014 - May 2014: Cape Town, South Africa
  • June 2014 - December 2014: San Francisco

As a result, I’m certainly not new to the idea of traveling. At the same time, I had been pretty settled in San Francisco for most of the last 2 years with some traveling around our team retreats. To give up my apartment and become a full digital nomad was an extra step. Here’s what made me take that step:

I feel like there’s so much to see, and I want to explore more while I’m (somewhat) young and single and have the flexibility

I started Buffer when I was 23 and I literally felt like I’d live forever back then, and that I don’t age. Having worked on Buffer for almost 5 years, I’ve realized that is quite a long time, and I’ve been getting older during those years. I expect that naturally I might be in a position some time in my thirties where I’ll want to settle in one place. In the meantime, I feel like there is so much of the world to explore, and I want to get out there and see it.

I have the opportunity to be an example of a whole new way of living your life

“Observe the masses and do the opposite.” - James Caan

A theme for my life for the last 5 years while building Buffer has been to always take the path less traveled, both personally and as a company. That’s how we ended up choosing to be super transparent, work as a distributed team, do a very unconventional $3.5m round of funding, be self-managed with no bosses amongst other less traditional choices.

Therefore, I felt a strong urge and that I might regret it if I don’t take this opportunity to become a digital nomad and be an example of a whole new way of living. It’s currently very rare to live in this way, moving around the world and working, with all your belongings in a single bag. Not only is it already rare to be a digital nomad, it felt less common still to be a digital nomad as part of a larger team with VC funding. I felt like it could be great for me to be an example of this being possible, and to explore it and share my learnings. Of course, it’s a lot of fun too.

I wanted to try truly experiencing solo travel

In my many travels in the last 5 years, I’ve always traveled with others (usually my co-founder Leo) other than one trip to Asia. I had read a lot about the joys (and the challenges) of solo traveling and I wanted to experiment with it. I found myself in a position where Leo was interested in travel, but not until later in the year, and he was focusing on building himself into communities more in San Francisco (something I admire, and will later describe, is a challenge I have).

The situation posed the perfect chance for me to try solo traveling. I felt especially excited as an introvert who feels quite happy to be alone. Solo traveling felt like it provides the perfect balance of being able to always find the alone time I need, but also being very incentivized to get out and meet new people myself, since I don’t have someone I know to rely on for my need for socializing. I actually find it exciting and much easier to meet new people when I’m by myself.

Some of the high points and successes in my 3 months of travel

Looking back, it was an incredible 3 months, a period of time I think I will long remember. Here are some of the high points:

1. I spent a month traveling with my friend and co-worker Brian, it was so much fun

If you have the opportunity to travel with a friend, be sure to take it. I was already great friends with Brian, but I think traveling around Asia with him for a month really gave us a chance to get to know each other even better. There were so many fun things we experienced together, like a traditional sumo wrestling practice, getting drinks with Japanese and struggling with the language barrier, traveling out to the North/South Korea demilitarized zone, and many more. I think we’ll both always look back on and laugh about some of those awesome times. What’s more, I think it makes our working relationship better too.

2. Experiencing some of the top cultural landmarks and sights in the world, all in just a few months

“A new psychology study suggests that buying life experiences rather than material possessions leads to greater happiness for both the consumer and those around them.” ScienceDaily

On the whole, I worked a normal week most weeks, and I did all of my travel between places and relocating to new accommodation on weekend days. So, I maintained a decent level of productivity (more on that later). Despite that, I had the incredible chance to fit in a crazy number of experiences into the 3 month period.

In the 3 month period, I had a chance to experience some absolutely incredible sights. The view from the Tokyo Skytree was awesome. I visited several temples in both Tokyo and Seoul. I had dinner at a ninja themed restaurant. I had drinks on top of the Marina Bay Sands in Singapore. I experienced Ludovico Einaudi in the Sydney Opera House and saw a movie at an open air cinema with a view of the Opera House and the Sydney Harbour Bridge. I went surfing at Bondi Beach and Manly Beach in Sydney and at Waikiki and Diamond Head in Hawaii. I went for evening walks along Santa Monica beach. I ate breakfast in Beverly Hills and saw the Hollywood Sign. I experienced the SXSW conference and had dinner with Eric Ries, Tim O’Reilly and others in Austin, and I went to a Rodeo in Houston. And that’s cutting the list short.

I’m very aware how lucky I am to experience all of this. Many days I wake up and can’t quite believe it. I would guess that for many, this could be a list of things you’d see in a lifetime. It was truly a highlight to see so much in such a short space of time, and kept me energized.

When we did our $3.5m funding round at the end of last year, Leo and I were lucky to each sell a small portion of our shares and receive liquidity. I’m particularly happy that so far I’ve spent zero on any substantial new material possessions, and the only spending I’ve done has been on travel and experiences, as well as some investments. It’s early to tell, but so far this feels like one of the best uses for money. That doesn’t mean I’ve spent a lot on travel or these experiences. I believe this kind of travel is less out of reach than many people think.

3. Meeting lots of new people and catching up with friends

The cool thing about being in a new place is that you can’t help but meet new people. I find that I have this energy and excitement whenever I set foot in a new city, I feel like just the way I walk around with that extra curiosity and enthusiasm makes me more likely to get talking with people. I also find I’m more eager to reach out and meet people, whether by Tweeting that I’m around, or by meeting people through an existing friend in the city.

It was so much fun to catch up with old friends in almost all the cities I was in, and through those people meet new friends who I will stay in touch with for years to come. And one thing I’ve found in the past is that we live in a time where many people travel, and so it’s not at all out of the question that I’ll be hanging out with some of these people in a completely different city in the future.

4. Keeping up my gym routine while traveling

One of the things I was happiest about while traveling was that I almost completely kept up my gym routine. I found an awesome Gold’s Gym in Tokyo. In Seoul I struggled and found that there aren’t too many gyms, but once I arrived in Singapore I was eager to get back to my exercise routine and signed myself up for a 2 week pass at Fitness First and went several times a week.

All in all, I had 31 gym sessions during the 12 weeks, which is an average of about 2.5 sessions a week. I generally aim for 3-4 sessions a week, so this felt like a pretty good effort and outcome amongst all the challenges of being in a new place, finding a gym and having so many other things I also wanted to do and see.

In the last couple of years, I’ve generally focused solely on strength training, and enjoyed that a lot. In the last 3 months I also started doing some cardio again with a little running and more recently some high intensity interval training through tabata sprints. I added cardio and some bodyweight exercise to my strength training. I’ve been working towards achieving a muscle up for several months and went regularly to the outdoor gym at Bondi Beach in Sydney and continued my practice and finally achieved my first muscle up at Original Muscle Beach in Santa Monica.

5. Being in a new place and experiencing different cultures made me more open minded again

One of the things I didn’t anticipate, but in hindsight makes complete sense, is how much traveling would affect my interests and focuses. It’s something I’ve grown to love and crave traveling for.

For example, when I was in Japan, I naturally got very interested again in improving my Japanese, and I was able to practice it quite a lot (I lived in Japan for 3.5 years as a child, and tried my best to keep it up by studying it for 3 years alongside my Computer Science degree, but have let the language slip away quite a lot).

Another thing that happened in Japan was that I had the chance to meet a lot of Japanese Buffer users, and I realized how important localization might be for us to implement. I then proceeded to propose a task force within the team to work on localizing Buffer (as an update, that task force was put on hold to build Buffer for Pinterest, and may continue soon).

A final example is that when Brian and I were in Seoul, we visited the North/South Korea demilitarized zone and I was very motivated to learn about the history of Korea while I was there. I read Nothing to Envy: Ordinary Lives in North Korea, which I thoroughly enjoyed and found fascinating, and watched a couple of TED talks (here and here) by North Korean defectors.

I feel super lucky and find it very fun to learn about topics like this while also experiencing the actual place where the events happened.

6. I did a lot of speaking events while traveling, I was happy to be able to help many people this way

One of my favorite things to do is to be able to give back. I’ve written before that I’ve found helping others brings me a lot of happiness. In addition, as I’ve been lucky to be part of Buffer growing more successful, I’ve also experienced growing requests from people asking my advice on things. It’s got to the point where I don’t have the time to respond to every request, which is something I struggle with since I’d love to help everyone.

One great way I’ve found to scale my ability to help people is through speaking events, blogging and other ‘one to many’ methods. Additionally, I found that being in Asia and having only a week in each place, setting up some events was one of the best ways to be able to meet everyone who was interested in speaking to me.

The other key thing that came to my mind in the weeks up to leaving for the trip was that as a fully distributed team, one of the areas of the world where we have the least people is Asia. As a result, I think it can be a little more lonely for team members in that timezone, and also means as a company we’re less open minded to some of the cultural differences both on a team dynamics and a market level. I decided to take the opportunity to try to spread word of Buffer, and ended up with quite a solid schedule of speaking over the few months:

  • Ad-hoc Buffer meetup in Tokyo
  • Fireside chat in Singapore
  • Fireside chat at StartupLokal event in Jakarta
  • Speaking at SaaSBusinessAsia conference in Singapore
  • Buffer Sydney meetup fireside chat event with Leo
  • Speaking on Open Pay panel at SXSW in Austin

It was a lot of fun to speak at all these events and meet hundreds of people through them.

As an introvert, I have to be quite mindful of my own energy levels when I’m speaking a lot, and also aware of how much time it takes me to feel well prepared for speaking events. I generally try to do fireside chats if it’s a more ad-hoc event, since I find those a lot easier to do on the fly and still feel they’re providing a lot of value for people. I loved doing all these events, however I think in the future I might not pack as much into a short space of time, since I think it was somewhat overwhelming at times and I think it impacted how productive I could be with all the other tasks I had going on at Buffer during that time.

The biggest challenges of being in 11 cities in 3 months, and the digital nomad lifestyle

A key reason I wanted to write this post and document the experiences I had while they’re fresh in my mind, is that despite having the incredible privilege to travel across 3 continents in 3 months and have some massive highs, there were in fact some real challenges and low points. I feel it’s important to share that side of the story, and hopefully it can be interesting and useful for somebody.

1. At times my productivity suffered and I felt I wasn’t as present as I should have been for Buffer

I mentioned earlier that I traveled and relocated to new accommodation on the weekends, and I worked regular weeks for the full 3 month period. This went quite far in helping me to stay relatively productive during these travels.

At the same time, being in a new place means adjusting to many new things, even as simple as finding grocery shopping and food places. Everything takes a little longer than what you’ve become used to in a place you’ve had months or years to become familiar and comfortable with, and that can be a little frustrating if you don’t anticipate it. As a remote worker who enjoys the coffee shop environment to get things done, I also found that I could often get to a coffee shop which wasn’t an ideal setup or where the wifi was not quite fast enough, and so it could take a couple of attempts before I found a great one. That took away yet more time.

All in all, I do see the travels as somewhat of a failure with regards to my productivity and my contribution to Buffer. I’m not a student taking a year off to travel the world once before settling into work, this is instead something I’m working towards finding balance so it can be much more long-term. I don’t have a throwaway traveling job just to get by, I’m the CEO of a company with venture financing and I have a lot of personal ambition to take Buffer much further than where it is right now. Therefore, daily routine and overall focus is crucial to having fulfillment, and with so much travel in a short space of time, I couldn’t quite hit the flow that I feel I need.

Thankfully, I’ve been able to take these learnings and bounce to a new situation fairly quickly. Since choosing to adjust to ‘slow travel’ (more on that below) and stay in Hawaii for 4-5 months, I’ve hit possibly my best flow in years, both in terms of my work on Buffer and my fitness goals. I will always be someone who likes to challenge myself and push towards limits in order to learn. In some ways I see this compressed travel as similar to my experiment of working 7 days a week, which also resulted in some great learnings.

2. One or two weeks in a place is not long enough to build lasting friendships or understand the culture beyond the surface

I’ve learned as a result of experimenting with 1-2 week visits compared to 3-6 month slow travel, that whenever I have the choice from now on, I will always take the option to stay in a single place for a few months.

Beyond the productivity struggles that come with being somewhere only for 1-2 weeks, it is also not long enough to create true new friendships or relationships. It’s almost impossible to sustain this for a long period of time and also have any sense of community. It was a lot of fun, however as the travels went on I found myself craving that sense of community, being able to hang out with people that know me well. As an introvert, I find that I naturally get drained when I spend a lot of time with other people, and even more so when I’m constantly meeting new people.

In addition to the challenge of having friends and that sense of community, I believe that part of the joy of travel is to experience, understand, and be changed by different cultures. For myself, I’ve found that I really can’t start to understand the culture of a new place unless I “live” there, and I think it takes at least 3 months, maybe 6, for things to start clicking. I like to feel like I’ve truly lived somewhere, been a part of it, and hopefully even had some tiny impact on it for the better.

3. I was hit with loneliness and had several times I felt down

It seems almost crazy that I could be literally traversing 3 continents and visiting many places in the world that people dream of experiencing, and feel down. I felt almost guilty for feeling it at times, that it was a lack of gratitude.

For most of the 3 months I felt absolutely incredible, and had an awesome time. During my time traveling Asia during January, I didn’t feel lonely at all, because I was traveling with Brian. For the first half of February while I was in Sydney, I was with the rest of the Buffer team on our 5th team retreat and several people stayed in Sydney afterwards, so I felt great then too. It was the last few weeks in Sydney when I was there by myself, and then during my two weeks in Santa Monica that the loneliness hit me a few times.

It was a little scary to feel myself affected by this. Some days I lost several hours where I was just feeling down and procrastinating. I’ve had a couple of other experiences of feeling down for one reason or another in the past, but it had been over 5 years since I had any feelings like this, so it came as quite a shock.

I’ve realized that a key challenge as a digital nomad is loneliness, and in many ways my traveling lifestyle of the last few years has left me without many strong friendships or relationships. This being my first time solo traveling also brought this out even more for me, I think.

I’m generally quite a pragmatic person. I reflect a lot, which can sometimes make me dwell on something and feel even worse about it. However, this reflection often helps me pinpoint the cause and act on it. In this case, I instantly started making a big effort to meet new people, and I also chose to stay in Hawaii for several months in order to build some longer term friendships. The result is that I’ve been able to completely turn this feeling around within a month and a half, and haven’t felt down for weeks now. I also found that keeping up my exercise routine helped me immeasurably during the ‘downs’, by gaving me something to regularly get a win with (and the endorphins released). I never felt down when I was exercising, and it often triggered a high that lasted several hours afterwards.

3 key learnings I’m taking forward for future travel and being a digital nomad

To finish up, I want to share a few observations and learnings I want to take forward for myself:

1. Travel is incredible

“Travel is fatal to prejudice, bigotry, and narrow-mindedness, and many of our people need it sorely on these accounts. Broad, wholesome, charitable views of men and things cannot be acquired by vegetating in one little corner of the earth all one’s lifetime.” - Mark Twain

I truly believe that the travel in the last few years has changed me for the better. If you have a chance to travel, I strongly urge you to take it. All the better if you can do it long-term in a sustainable way while working. Even short term travel is great, but if you can make it a lifestyle for even just a year or two, I think that’s when it becomes most powerful and fulfilling.

One of the best things about travel, and especially solo travel, which I’ve discovered in the last few months is how much you learn about yourself. I especially learned how to recharge and maintain energy and happiness, which came through experiencing both extremes of spending too much time with people as well as a few moments of real loneliness. I now feel much better equipped to strike that balance.

2. It’s important to know your purpose for travel, and your other chosen commitments

Whenever you choose to go traveling, you’re in a very unique position that applies only to you. We’re all different, and I think any sweeping advice is not wise.

I think it makes sense to think about what your own situation is. Are you young and focused purely on the travel, happy to do whatever job to just get by? Or do you already have your dream job and are striking the balance between the work you love and the destinations you want to see?

For me, I love working on Buffer, I couldn’t imagine a better job in the world. I also feel a big calling to see where we can take Buffer in the coming years. As a result, I plan to be very disciplined in the future about choosing my travel schedule. It’s important for me that I can spend the time I desire on Buffer, alongside seeing a new place.

3. For me, ‘slow travel’ is my preferred way to travel and be a digital nomad

Probably the most clear learning and conclusion for me of the 3 months of travel is that ‘slow travel’ is the perfect setup for me. By ‘slow travel’, I mean staying somewhere for at least 3 months, and generally 5-6 months or more. I’ve learned this for myself before in some casual ways, I even wrote about it a year ago. I feel like I’ve now truly pushed limits and experienced all options.

Most of these 3 months were short-term travel. Since then, I’ve been living in Hawaii for the last month and a half. I’ve found my flow and had some of my most productive weeks both on Buffer and with my exercise routine. I’ve met people who I’ve hung out with several times and hope some may become lifelong friends. This, for me, is what traveling is all about. This is my new plan.

What are your experiences of travel? Have you tried long-term travel, or do you want to? I’d love to hear from you in the comments!

Top photo credit: Andym5855. Rest are my own.